15,626

Caroline County, MD Homes

Section Image Section Image
    • /28

      Est $221,859

      Not Listed For Sale

      115 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      115 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

  • /25

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,539 Sq Ft

    306 Sunrise Ave, Ridgely, MD 21660

    Charming & Move-In Ready in Ridgely! This 4-bedroom, 2-full-bath home is priced to sell and ready for its next owner. New $25,000 roof with 50-year transferable warranty! Situated on a spacious corner lot in the friendly town of Ridgely, MD, the property includes 2 utility sheds for extra storage and plenty of parking with off-street spaces in both the front and rear, plus additional on-street

    Vincent De Lorenzo Samson Properties

    306 Sunrise Ave, Ridgely, MD 21660
  • /29

    $325,000

    Sold Oct 06, 2025

    614 Market St, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,508 Sq Ft
    • Built 1890

    Last Sold Summary

    • $130/SF
    • 53 Days On Market

    Current Estimated Value $334,719

    Last Listing Agent Michael Bozek Michael J. Bozek

    614 Market St, Denton, MD 21629
    • /8

      Not Listed For Sale

      0 Houston Branch Rd Unit MDCM2005056, Federalsburg, MD 21632

      0 Houston Branch Rd Unit MDCM2005056, Federalsburg, MD 21632

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Benjamin Alder The Land Group

  • /47

    $644,995

    • 4 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    4757 Long Swamp Rd, Federalsburg, MD 21632

    Welcome to 4757 Long Swamp Rd, a truly unique property in Federalsburg, MD, offering the perfect blend of equestrian facilities and comfortable country living on 7.04 acres. This well-maintained estate is ready for you and your horses, with no restrictions on property use and the added flexibility for the land to be subdivided. The grounds feature expansive pastures secured by electric fencing, a

    Billy Mister Keller Williams Realty

    4757 Long Swamp Rd, Federalsburg, MD 21632
  • /2

    $670,000

    Sold May 22, 2026

    12820 Porters Landing Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 2,676 Sq Ft
    • Built 1989

    Last Sold Summary

    • 11% Below List Price
    • $250/SF
    • 86 Days On Market

    Current Estimated Value $679,064

    Last Listing Agent Penny Hollis Samson Properties

    12820 Porters Landing Rd, Greensboro, MD 21639
    • /40

      Est $338,493

      Not Listed For Sale

      21968 Main St, Hillsboro, MD 21641

      • 4 Beds
      • 2 Baths
      • 2,704 Sq Ft
      • Built 1900
      21968 Main St, Hillsboro, MD 21641

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Ross Hunsberger Coldwell Banker Realty

  • /58

    $620,000

    • 4 Beds
    • 2.5 Baths
    • 2,704 Sq Ft

    16881 Heritage Hills Ln, Henderson, MD 21640

    Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a quiet drive, 16881 Heritage Hills Ln provides the perfect blend of seclusion, functionality, and room to grow. Best of all, there's no HOA, giving you the freedom to truly enjoy your property. Built in 2005, the home offers 2,704

    Kaitlyn Collins Benson & Mangold, LLC

    16881 Heritage Hills Ln, Henderson, MD 21640
  • /20

    $266,990

    Sold Oct 10, 2025

    120 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $252/SF
    • 24 Days On Market

    D.R. Horton Kinnamon Meadows

    120 Parkland Rd, Greensboro, MD 21639
    • /79

      Est $530,018

      Not Listed For Sale

      13056 Hog Lot Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2008
      13056 Hog Lot Rd, Ridgely, MD 21660

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Michele Williams Redfin Corp

  • /14

    $110,000

    $40K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    **Back Active at no fault of the seller**Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /2

    $348,000

    Sold Jun 03, 2026

    22650 Tanyard Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1964

    Last Sold Summary

    • 7% Above List Price
    • $300/SF
    • 7 Days On Market

    Current Estimated Value $340,226

    Last Listing Agent Valerie Brown Coldwell Banker Realty

    22650 Tanyard Rd, Preston, MD 21655
    • /24

      Not Listed For Sale

      123/123A/125 123A/12 N Main St, Federalsburg, MD 21632

      • Studio
      • 3,926 Sq Ft
      • Built 1895
      123/123A/125 123A/12 N Main St, Federalsburg, MD 21632

      Last Sold Summary

      • 125 Days On Market

      Last Listing Agent Barton Johnson/not int Marshy Hope Realty LLC

  • /64

    $527,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,942 Sq Ft

    8590 Briar Patch Dr, Denton, MD 21629

    Enjoy the space and privacy of this beautiful home situated on over 2 acres just outside of Denton. The main level features a formal dining room, a spacious primary suite with separate his-and-her closets, and a private bath with a walk-in shower. The kitchen opens to the family room, creating an inviting space for everyday living and entertaining.Custom window treatments enhance both the

    Barbara Blosser Long & Foster Real Estate, Inc.

    8590 Briar Patch Dr, Denton, MD 21629
  • 25999 Fox Grape Rd, Greensboro, MD 21639

    $379,000

    Sold Mar 20, 2026

    25999 Fox Grape Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 1987

    Last Sold Summary

    • $211/SF
    • 70 Days On Market

    Current Estimated Value $383,026

    Last Listing Agent Amy Betts Coldwell Banker Realty

    25999 Fox Grape Rd, Greensboro, MD 21639
    • /7

      Not Listed For Sale

      0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660

      0 Burnt Mill Rd Unit MDCM2004842, Ridgely, MD 21660

      Last Sold Summary

      • 124 Days On Market

      Last Listing Agent Stephan Strothe Washington Fine Properties, LLC

  • /28

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    14540 Drapers Mill Rd, Goldsboro, MD 21636

    Searching for your own private oasis with endless possibilities? Welcome to a rare 16.29-acre offering made up of four separate parcels, thoughtfully improved and ready for whatever vision you bring. Whether you dream of a hobby farm, a multi-use homestead, or a private retreat, this property delivers space, versatility, and infrastructure you won’t find anywhere else. Across the acreage you’ll

    Amanda Morgan Brenton Realty Group

    14540 Drapers Mill Rd, Goldsboro, MD 21636
  • /12

    $80,000

    Sold Jul 24, 2026

    103 Chambers St, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1900

    Last Sold Summary

    • 41% Below List Price
    • $54/SF
    • 210 Days On Market

    Last Listing Agent Pamela Geib Long & Foster Real Estate, Inc.

    103 Chambers St, Preston, MD 21655
    • /5

      Est $103,469

      Not Listed For Sale

      21373 Dover Bridge Rd, Preston, MD 21655

      • Built 1890
      21373 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /21

    $229,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    103 Riverwalk Terrace, Federalsburg, MD 21632

    Hurry before it’s gone! This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community.

    Kat Thompson Benson & Mangold, LLC.

    103 Riverwalk Terrace, Federalsburg, MD 21632
  • /46

    $348,000

    Sold Oct 14, 2025

    22490 Ash Blvd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2001

    Last Sold Summary

    • $188/SF
    • 22 Days On Market

    Last Listing Agent Kathryn Tennant Douglas Realty, LLC

    22490 Ash Blvd, Preston, MD 21655
    • /39

      Est $534,574

      Not Listed For Sale

      21303 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 3 Baths
      • 2,607 Sq Ft
      • Built 1998
      21303 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /47

    $509,900

    • 4 Beds
    • 3.5 Baths
    • 2,231 Sq Ft

    14631 Fox Chase Cir, Ridgely, MD 21660

    OPEN House this Saturday Aug. 1, 3:30-5:30pm! Welcome home to your own private country paradise. Nestled on 2.43 peaceful acres, this beautifully renovated log cabin blends rustic charm with modern comfort. Designed to impress, the home features both a main-level primary suite and a spacious second-floor primary suite, offering exceptional flexibility for family or guests. Thoughtfully updated

    Rick Parreco RE/MAX Executive

    14631 Fox Chase Cir, Ridgely, MD 21660
  • /35

    $239,900

    Sold Mar 31, 2026

    515 Vaughn Ave, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 1,756 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Below List Price
    • $137/SF
    • 27 Days On Market

    Current Estimated Value $245,197

    Last Listing Agent Chad Muse KD Realty Inc

    515 Vaughn Ave, Greensboro, MD 21639
    • /23

      Est $317,187

      Not Listed For Sale

      106 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1995
      106 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Sid Campen Charles C. Powell, Inc. Realtors

  • /55

    $635,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    11142 Log Cabin Rd, Denton, MD 21629

    Welcome to 11142 Log Cabin Road! This unique property offers the perfect combination of residential living and valuable commercial space, all on one expansive, 4.53 acre lot. This beautiful colonial-style home has great curb appeal with its classic look, neatly trimmed landscaping, and a spacious front yard shaded by mature trees. The main home spans over 2,700 square feet and features four

    Courtney Gallagher Keller Williams Realty Central-Delaware

    11142 Log Cabin Rd, Denton, MD 21629
  • /29

    $261,000

    Sold Jan 13, 2026

    1105 Market St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 2021

    Last Sold Summary

    • $201/SF
    • 85 Days On Market

    Current Estimated Value $277,652

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    1105 Market St, Denton, MD 21629
    • /53

      Est $437,767

      Not Listed For Sale

      230 Main St, Preston, MD 21655

      • 5 Beds
      • 5 Baths
      • 3,208 Sq Ft
      • Built 1890
      230 Main St, Preston, MD 21655

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Shane Slacum LPT Realty, LLC

  • /22

    $174,000

    $15K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    Move-In Ready & Beautifully Remodeled!This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality.The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One

    Dawn Hubbard Keller Williams Select Realtors of Cambridge

    107 Smith St, Federalsburg, MD 21632
  • /48

    $350,000

    Sold Jan 14, 2026

    334 Deep Shore Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Built 1957

    Last Sold Summary

    • $213/SF
    • 15 Days On Market

    Current Estimated Value $345,058

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    334 Deep Shore Rd, Denton, MD 21629
    • /17

      Est $299,272

      Not Listed For Sale

      104 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft
      • Built 1995
      104 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Amy Endzel Keller Williams Select Realtors of Annapolis

  • /2

    $25,000

    Pending
    • Land
    • 22,651 Sq Ft
    • $48,077 per Acre

    10291 Bridge St, Denton, MD 21629

    1/2 ACRE LOT IN DENTON. THIS PROPERTY WAS PURCHASED THROUGH TAX SALE, SELLER IS BRYNN, LLC.

    Henry Gibbons-Neff Meredith Fine Properties

    10291 Bridge St, Denton, MD 21629
  • /28

    $233,990

    Sold Aug 20, 2025

    124 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $171/SF
    • 20 Days On Market

    D.R. Horton Riverwalk Terrace

    124 Julie Ln, Federalsburg, MD 21632
    • /14

      Est $389,798

      Not Listed For Sale

      111 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft
      • Built 1974
      111 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 323 Days On Market

      Last Listing Agent Barbara Nichols Results Realty Inc.

  • /27

    $265,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well, Septic has been inspected and is in acceptable working condition. Stones have been added to the driveway . A few more touches and it is move in ready. Don't wait to view this Newley redone home.

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /39

    $365,000

    Sold Mar 27, 2026

    24029 Meadows Dr, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 1990

    Last Sold Summary

    • $204/SF
    • 67 Days On Market

    Current Estimated Value $370,364

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    24029 Meadows Dr, Ridgely, MD 21660
    • /14

      Est $404,416

      Not Listed For Sale

      107 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 2023
      107 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 154 Days On Market

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /2

    $95,000

    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    310 E Central Ave, Federalsburg, MD 21632

    Excellent investment opportunity! Over 1/4 acre lot. Home needs TLC. Partial owner financing available. Call for more info. This deal will not last long. Grab it while you have the chance!

    Raphael Szendro R&R Executive Realty

    310 E Central Ave, Federalsburg, MD 21632
  • /20

    $267,490

    Sold Aug 12, 2025

    124 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $253/SF
    • 6 Days On Market

    D.R. Horton Kinnamon Meadows

    124 Parkland Rd, Greensboro, MD 21639
    • /37

      Est $398,675

      Not Listed For Sale

      1103 Trice Meadows Cir, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,816 Sq Ft
      • Built 2010
      1103 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

Showing Results 121 - 160, Page 4 of 18

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